User Experience consultant and digital product designer, New York City.

I have been successfully freelancing (or consulting as I like to say) for almost five years. Much earlier in my career I tried (and failed) at freelancing. I had just moved to New York and did not have a network of any kind really, which looking back on it – was really a rookie mistake. In addition, at the time - I wasn’t great at managing my time and never really never got enough work to make something take off. I tried again six years later and for a few really key reasons, was successful. In this post I’ll share what the key factors for my successful transition was. These reasons are repeatable and anyone with the determination and drive can do it. These are ordered in a sequence of what I think is most important.

Be Good at What You Do

“The skills to pay the bills!”

This one may seem obvious but it’s worth stating anyway. When I attempted freelancing for the first time, I wasn’t a great designer – I was barely good. I knew that I had a lot of room for improvement but I believed in my potential. Becoming better at what you do while freelancing can be a great way to learn but it also can create frictions that when paired with other key factors, can be debilitating. The friction it created for me was one of time: I could only work so fast at my very junior level. That meant that it took me a long time to create designs that I could present to clients and given that I couldn’t realistically charge that much it was just hard to make a living. It also left little time for networking and self-promotion, which had a compounding effect and made it difficult to bring in more work.

After a brief stint at working in a grocery store in an effort to support myself, I got my first break working at a digital advertising agency and spent the next five years at a few different full-time jobs working on becoming a better designer and communicator. By the time I decided to freelance full-time I had a lot more experience under my belt and more importantly was confident in myself. In my line of work being able to talk to clients, present work and define a successful project process are all necessary components and they’re all things that I started to learn while working for other people and honed and further developed on my own.

Have a Safety Net or Savings Account

One of the hardest things to let go of when transitioning to freelancing is the concept of a steady paycheck. Going from working full-time to freelancing can be a leap of faith. As humans we naturally give into and obsess over fearful thoughts in certain situations. It’s easy to let the fearful thought of losing a paycheck stop you from making life changing decisions. The upside is: you can always get another job. It’s good to be smart about how you transition though. If you have a little money in the bank it will go a long way in allowing you to focus on your real goals and will alleviate some of the stress of worrying about when the next good paying project will come in. How much of a safety net really depends on your personal situation and cost of living. If you really want to do due diligence, understand your true cost of living and project out your financial life in a spreadsheet.

Have a Network or a Few Existing Clients

Not having either of this things was one reason for my first attempt at freelancing not working out. It was doubly tough for me as I moved to a new city (New York City) and tried freelancing at the same time. The ideal scenario in a freelancing situation is that you don’t have to go hunt and peck for work. So, if you’re good at what you do and you’re in a market where the supply and demand is in your favor then you really should have no problem getting work. However, there is one key: you have to put yourself out there and be willing to self-promote. This upside to self-promoting is work will more naturally come to you. I self-promote in a few simple ways: my Website (which is very informational) and uses simple SEO, through the articles on my blog – like the one you’re reading now and I tweet a lot about industry stuff. Tweeting has less to do with obtaining clients and more to do with just being part of the design community.

Before I made the decision to freelance full-time I spent a couple years moonlighting and while working full-time. This can be exhausting and some jobs don’t like or allow you to do this so you should be careful but it’s a great way to take the skills you learn on the job and start to apply them on your own to your own work. In my opinion this can make you a better designer at your full-time job because you inevitably pick up new things while freelancing that you can apply to your projects at work. Passion or hobby projects are another great way of doing this.

What it came down to for me was, the timing was right. Not only did I have a good, balanced skill set but I already had a few clients when I made the transition, making it very smooth – in fact, I didn’t even take one day off! My last day at my last job was Friday and I started my first project as a full-time freelancer on Monday.

Maintaining Your Mojo!

Successfully transitioning to a full-time freelance career but maintaining it is another. Here are a few quick tips and recommendations on how to pave a successful path.

Treat People Right

Design is a service oriented business and relationships are what matter most. Much of your success as a freelancer is created by how you make people feel. Do people feel good during and after working with you? If they do, they are highly likely to recommend you. Customer service is a big part of any successful business. It’s not just one thing that creates a good customer service, in my experience it’s usually a handful of things such as: responding timely to emails, being open to feedback, being a good communicator, making it easy for your client to be part of the process and provide feedback, sending calendar invites and so on. If you can’t do these things you’ll have to work harder to be successful. Having a sense of humor and giving small, thoughtful gifts from time-to-time are big plusses!

Properly Scope Projects

This is something that can take some time to master but once you do – it really pays off. It pays off because it allows you to realistically manage your time, it builds confidence with your clients and is the start of any successful project. To properly scope a project you first have to have proper insight – enough insight to put a project plan together including most importantly a timeline and the deliverables within that timeline. If a project goes off the rails for any reason it’s best to own up to it (as soon as possible), apologize and do whatever it takes to get it back on track. Unless of course your client and or something out of your control is a significant part of why the project went off the rails.

Evaluate & Update Your Process When Necessary

At this point in my career I have a pretty solid process that I can tweak or customize per client or project but I’m always reevaluating in an effort to make sure I’m working in the smartest most efficient way possible. How I work now and the tools are use are very different from three or four years ago. All these things impact the client experience. I work primarily with startups and one thing all startups have in common is a lack of time. This means that I have to make the process easy and not time consuming, which means I put thought into how often I’m contacting them, when and how often we meet and the structure of those meetings to ensure we make the most of our time together.

In Summary

Freelancing can be a very rewarding and fun way to make a living while at the same time living your life. In my experience, it’s one of the best ways to grow as a person and create your own personal brand equity. Successful work starts with having some control over the process; although full-time jobs can offer this, when you freelance you’re in the driver’s seat 100% of the time and you can do things your way and pivot in real-time with zero red tape. It’s empowering and exciting.